WO2020009519A1 - 다환 화합물 및 이를 포함하는 유기 발광 소자 - Google Patents

다환 화합물 및 이를 포함하는 유기 발광 소자 Download PDF

Info

Publication number
WO2020009519A1
WO2020009519A1 PCT/KR2019/008276 KR2019008276W WO2020009519A1 WO 2020009519 A1 WO2020009519 A1 WO 2020009519A1 KR 2019008276 W KR2019008276 W KR 2019008276W WO 2020009519 A1 WO2020009519 A1 WO 2020009519A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
unsubstituted
layer
light emitting
Prior art date
Application number
PCT/KR2019/008276
Other languages
English (en)
French (fr)
Korean (ko)
Inventor
정민우
이동훈
장분재
이정하
한수진
박슬찬
황성현
Original Assignee
주식회사 엘지화학
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201980034691.8A priority Critical patent/CN112204026B/zh
Publication of WO2020009519A1 publication Critical patent/WO2020009519A1/ko

Links

Images

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers

Definitions

  • the present specification relates to a polycyclic compound and an organic light emitting device including the same.
  • an organic light emitting device is a light emitting device using an organic semiconductor material, and requires an exchange of holes and / or electrons between an electrode and the organic semiconductor material.
  • the organic light emitting device can be classified into two types according to the operation principle. First, an exciton is formed in the organic layer by photons introduced into the device from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is a light emitting element of the form.
  • the second is a light emitting device in which holes and / or electrons are injected into the organic semiconductor material layer that interfaces with the electrodes by applying voltage or current to two or more electrodes, and is operated by the injected electrons and holes.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • organic light emitting devices When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows.
  • organic light emitting devices are known to have characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.
  • Materials used as the organic material layer in the organic light emitting device may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on their functions.
  • the luminescent material includes blue, green, and red luminescent materials and yellow and orange luminescent materials necessary to realize better natural colors depending on the emission color.
  • a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
  • the principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to give high efficiency light.
  • the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
  • a material forming the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material.
  • a hole injection material such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc.
  • An exemplary embodiment of the present specification is to provide a compound represented by the following formula (1).
  • Ar1 and Ar2 each independently represent a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted pyrenyl group; Substituted or unsubstituted perenyl group; Substituted or unsubstituted triphenyl group; Substituted or unsubstituted chrysenyl group; A substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted heterocyclic group,
  • L is a substituted or unsubstituted arylene group; A substituted or unsubstituted divalent dibenzofuran group; A substituted or unsubstituted divalent dibenzothiophene group; Or a substituted or unsubstituted divalent carbazole group,
  • a is an integer of 1 to 3
  • L in parentheses is the same as or different from each other
  • Ar3 is the following Chemical Formula 2,
  • n is an integer from 2 to 5
  • Ar3 in parentheses is the same as or different from each other,
  • Y is O; Or S.
  • the first electrode A second electrode provided to face the first electrode; And an organic light emitting device including at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.
  • the compound described herein can be used as the material of the organic material layer of the organic light emitting device.
  • the compound according to at least one embodiment may improve the lifespan characteristics or in the organic light emitting device.
  • the compounds described herein can be used as materials for light emitting layers, electron transport layers, electron injection layers and the like.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
  • the present specification provides a compound represented by Chemical Formula 1.
  • the compound represented by Formula 1 is used in the organic material layer of the organic light emitting device, the efficiency of the organic light emitting device is always.
  • substituted means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is replaced, that is, a position where the substituent can be substituted, if two or more are substituted , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted is deuterium; Halogen group; Cyano group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents.
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
  • examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms.
  • alkyl group examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group and n-jade Although there exist a tilt group etc., it is not limited to these.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group and the like, but is not limited thereto.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group.
  • the arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
  • arylamine group examples include phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 3-methyl-phenylamine group, 4-methyl-naphthylamine group, 2-methyl-biphenylamine Groups, 9-methyl-anthracenylamine groups, diphenyl amine groups, phenyl naphthyl amine groups, biphenyl phenyl amine groups, and the like, but are not limited thereto.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a monocyclic aryl group, but may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, peryllenyl group, triphenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • Spirofluorenyl groups such as (9,9-dimethylfluorenyl group), and It may be a substituted fluorenyl group such as (9,9-diphenyl fluorenyl group).
  • the present invention is not limited thereto.
  • the heterocyclic group is a ring group containing one or more of N, O, P, S, Si, and Se as hetero atoms, and carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms.
  • the heterocyclic group include pyridyl group, pyrrole group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazole group, pyrazole group, dibenzofuranyl group, dibenzothiophenyl group, and the like. It is not limited only to.
  • heterocyclic group may be applied except that the heteroaryl group is aromatic.
  • adjacent The group may mean a substituent substituted with an atom directly connected to an atom in which the corresponding substituent is substituted, a substituent positioned closest in structural conformation to the substituent, or another substituent substituted in the atom in which the substituent is substituted.
  • two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" to each other.
  • ring in a substituted or unsubstituted ring in which adjacent groups are bonded to each other, a “ring” means a hydrocarbon ring; Or heterocycle.
  • the hydrocarbon ring may be an aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or aryl group except for the above-mentioned monovalent one.
  • the description of the aryl group may be applied except that the aromatic hydrocarbon ring is monovalent.
  • the heterocycle includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms include one or more atoms selected from the group consisting of N, O, P, S, Si, Se, and the like. can do.
  • the heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and the aromatic heterocycle may be selected from examples of the heteroaryl group except that it is not monovalent.
  • Ar1 and Ar2 are each independently, a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted pyrenyl group; Substituted or unsubstituted perenyl group; Substituted or unsubstituted triphenyl group; Substituted or unsubstituted chrysenyl group; A substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted heteroring group.
  • Ar1 and Ar2 are each independently, a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted phenanthrenyl group; Or a substituted or unsubstituted heteroring group.
  • Ar1 and Ar2 are each independently, a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted carbazole group.
  • L is a substituted or unsubstituted arylene group; A substituted or unsubstituted divalent dibenzofuran group; A substituted or unsubstituted divalent dibenzothiophene group; Or a substituted or unsubstituted divalent carbazole group.
  • L is a substituted or unsubstituted arylene group having 6 to 15 carbon atoms; Substituted or unsubstituted divalent dibenzofuran; Substituted or unsubstituted divalent dibenzothiophene; Or substituted or unsubstituted divalent carbazole.
  • L is a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Substituted or unsubstituted terphenylene group; Substituted or unsubstituted naphthylene group; A substituted or unsubstituted divalent phenanthrene group; Substituted or unsubstituted divalent anthracene group; A substituted or unsubstituted divalent dibenzofuran group; A substituted or unsubstituted divalent dibenzothiophene group; And a substituted or unsubstituted divalent carbazole group.
  • L may be selected from two or more substituents connected to each other.
  • L is a phenylene group; Biphenylene group; Terphenylene group; Naphthylene group; Divalent phenanthrene group; Divalent anthracene groups; Divalent dibenzofuran group; A substituted or unsubstituted divalent dibenzothiophene group; And a substituted or unsubstituted divalent carbazole group.
  • L may be selected from two or more substituents connected to each other.
  • a is an integer of 1 to 3.
  • a is 1.
  • L is a phenylene group; Biphenylene group; Terphenylene group; Naphthylene group; Divalent phenanthrene group; Divalent anthracene groups; Divalent dibenzofuran group; A substituted or unsubstituted divalent dibenzothiophene group; And a substituted or unsubstituted divalent carbazole group.
  • a is 2.
  • two L are connected, and it can be expressed as L1-L2.
  • L1 and L2 each represent a phenylene group; Biphenylene group; Terphenylene group; Naphthylene group; Divalent phenanthrene group; Divalent anthracene groups; Divalent dibenzofuran group; A substituted or unsubstituted divalent dibenzothiophene group; And a substituted or unsubstituted divalent carbazole group.
  • L1-L2 is a phenylene group-phenylene group; Naphthylene group-phenylene group; Phenylene group-naphthylene group; Divalent anthracene group-phenylene group; Phenylene group 2-valent anthracene group; Phenylene group divalent carbazole; Or a divalent carbazole-phenylene group.
  • a is 3.
  • two L are connected, and it can be expressed as L1-L2-L3.
  • L1 to L3 each represent a phenylene group; Biphenylene group; Terphenylene group; Naphthylene group; Divalent phenanthrene group; Divalent anthracene groups; Divalent dibenzofuran group; A substituted or unsubstituted divalent dibenzothiophene group; And a substituted or unsubstituted divalent carbazole group.
  • L1-L2-L3 is a phenylene group-phenylene group-phenylene group; Phenylene group-naphthylene group-phenylene group; Phenylene group-phenylene group-naphthylene group; Phenylene group 2-valent anthracene group-phenylene group; Or a phenylene group divalent carbazole-phenylene group.
  • n is an integer of 2 to 5. According to n, since the number of Ar3 substituted by L is determined, L is (n + 1) specifically ,.
  • the number of Ar3 to be substituted for all two L is n, specifically, when a is 2, when two L represented by L1-L2, L1
  • the sum of the number of Ar3 substituted with and the number of Ar3 substituted with L2 is n.
  • the number of Ar3 to be substituted for all three L is n, specifically, when a is 3, when expressing three L as L1-L2-L3 Is the sum of the number of Ar3 substituted by L1, the number of Ar3 substituted by L2, and the number of Ar3 substituted by L3.
  • n is 2.
  • n is three.
  • n 4.
  • n is 5.
  • Ar3 is represented by the following formula (2).
  • Y is O; Or S,
  • Y is O.
  • Y is S.
  • Formula 1 is represented by any one of the following structures.
  • Compound of Formula 1 according to an exemplary embodiment of the present specification may be prepared by the production method described below.
  • the conjugation length of the compound and the energy bandgap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap.
  • a compound having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above.
  • the HOMO and LUMO energy levels of the compound may be controlled by introducing various substituents into the core structure of the above structure.
  • the compound which has the intrinsic property of the introduced substituent can be synthesize
  • a substituent mainly used in the hole injection layer material, the hole transport material, the light emitting layer material, and the electron transport layer material used in the manufacture of the organic light emitting device into the core structure, it is possible to synthesize a material satisfying the requirements of each organic material layer. Can be.
  • the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of Formula 1.
  • the organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that at least one organic material layer is formed using the above-described compound.
  • the compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating and the like, but is not limited thereto.
  • the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers.
  • the organic material layer may include an electron transport layer or an electron injection layer, the electron transport layer or an electron injection layer may include a compound represented by the formula (1).
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1 as a host of the light emitting layer.
  • the organic material layer including the compound represented by Chemical Formula 1 includes the compound represented by Chemical Formula 1 as a host, includes a fluorescent host or a phosphorescent host, and other organic compounds, metals, or metal compounds. May be included as the dopant.
  • the organic material layer including the compound represented by Chemical Formula 1 may include the compound represented by Chemical Formula 1 as a host, include a fluorescent host or a phosphorescent host, and may be used with an iridium-based (Ir) dopant. have.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode and the second electrode is an anode.
  • the organic light emitting diode may have a laminated structure as described below, but is not limited thereto.
  • the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1.
  • the compound may be included in the light emitting layer (3).
  • anode 2 illustrates an organic light emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 are sequentially stacked on a substrate 1.
  • the structure is illustrated. In such a structure, the compound may be included in the emission layer 7 or the electron transport layer 8.
  • the organic light emitting device uses a metal vapor deposition (PVD) method such as sputtering or e-beam evaporation, and has a metal oxide or a metal oxide or an alloy thereof on a substrate. It can be prepared by depositing an anode to form an organic material layer including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • PVD metal vapor deposition
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure.
  • the organic layer may be prepared by using a variety of polymer materials, and by using a method such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in layers.
  • the anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection material is a material capable of well injecting holes from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer.
  • the hole injection material include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transporting material a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable.
  • a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable.
  • Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • An electron blocking layer may be provided between the hole transport layer and the light emitting layer.
  • the electronic blocking layer may be a compound described above or a material known in the art.
  • the emission layer may emit red, green, or blue light, and may be formed of a phosphor or a fluorescent material.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • Alq 3 8-hydroxyquinoline aluminum complex
  • Carbazole series compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzo quinoline-metal compound
  • Benzoxazole, benzthiazole and benzimidazole series compounds include Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • PSV poly (p-phenylenevinylene)
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Iridium complex used as the dopant of the light emitting layer is as follows, but is not limited thereto.
  • the electron transporting material a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is suitable.
  • Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the hole blocking layer is a layer for blocking the arrival of the cathode of the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.
  • the organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • compound A-1 (25.5 g, 67.5 mmol), bis (pinacolato) diboron (18.8g, 74.2 mmol) and potassium acetate (13.2 g, 134.9 mmol) are mixed and added to 200 ml of dioxane Heated with stirring.
  • bis (dibenzylideneacetone) palladium (6 g, 1.1 mmol)
  • tricyclohexylphosphine 0.6 g, 2.2 mmol
  • compound B-1 In a nitrogen atmosphere, compound B-1 (28.0 g, 80.9 mmol), bis (pinacolato) diboron (22.6 g, 89.0 mmol) and potassium acetate (15.9 g, 161.8 mmol) were mixed and added to 200 ml of dioxane, Heated with stirring. At reflux, bis (dibenzylideneacetone) palladium (1.4 g, 2.4 mmol) and tricyclohexylphosphine (1.4 g, 4.9 mmol) were added thereto, and the mixture was stirred while heating for 3 hours. After the reaction was completed, the temperature was lowered to room temperature, followed by filtration.
  • Compound B-2 (28.7 g, 81%) was prepared by recrystallization with ethanol after distillation under reduced pressure.
  • compound F-1 (27.7 g, 67.4 mmol), bis (pinacolato) diboron (56.5 g, 222.4 mmol) and potassium acetate (39.7 g, 404.4 mmol) were mixed and added to 300 ml of dioxane, Heated with stirring.
  • bis (dibenzylideneacetone) palladium (1.2 g, 2.0 mmol) and tricyclohexylphosphine (1.2 g, 4.0 mmol) were added thereto, and the mixture was heated and stirred for 3 hours. After the reaction was completed, the temperature was lowered to room temperature, followed by filtration. Water was added to the filtrate, and the mixture was extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate.
  • Compound F-2 (23.2 g, 51%) was prepared by recrystallization with ethanol after distillation under reduced pressure.
  • the glass substrate coated with ITO (indium tin oxide) having a thickness of 1,300 kPa was put in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO indium tin oxide
  • Fischer Co. was used as a detergent
  • distilled water was filtered secondly as a filter of Millipore Co. as a distilled water.
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • the hole injection layer was formed by thermally vacuum depositing the following HI-1 compound to a thickness of 50 kPa on the prepared ITO transparent electrode.
  • a hole transport layer was formed by thermal vacuum deposition of the following HT-1 compound to a thickness of 250 GPa on the hole injection layer, and an electron blocking layer was formed by vacuum deposition of the following HT-2 compound to 50 GPa on the HT-1 deposition film.
  • ET-1 compound was vacuum deposited to a thickness of 250 kPa on the light emitting layer to form an electron transport layer
  • the following ET-2 compound and Li were vacuum deposited on the electron transport layer at a weight ratio of 98: 2 to form an electron injection layer having a thickness of 100 kW.
  • Aluminum was deposited on the electron injection layer to a thickness of 1000 ⁇ to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 ⁇ / sec
  • the aluminum was maintained at a deposition rate of 2 ⁇ / sec
  • the vacuum degree during deposition is 5 ⁇ 10 -8 ⁇ 1 ⁇ 10 ⁇ 7 torr was maintained.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound described in Table 1 below instead of compound 1 of Preparation Example 3 in Experimental Example 1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound described in Table 1 below instead of compound 1 of Preparation Example 3 in Experimental Example 1.
  • the compounds of CE1 to CE11 in Table 1 are as follows.
  • the organic light emitting diode was measured voltage and efficiency at a current density of 10mA / cm 2 , the lifetime was measured at a current density of 50mA / cm 2 and the results are shown in Table 1 below.
  • LT 95 refers to a time when the luminance becomes 95% of the initial luminance.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
PCT/KR2019/008276 2018-07-05 2019-07-05 다환 화합물 및 이를 포함하는 유기 발광 소자 WO2020009519A1 (ko)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201980034691.8A CN112204026B (zh) 2018-07-05 2019-07-05 多环化合物及包含其的有机发光二极管

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2018-0078350 2018-07-05
KR20180078350 2018-07-05

Publications (1)

Publication Number Publication Date
WO2020009519A1 true WO2020009519A1 (ko) 2020-01-09

Family

ID=69059687

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2019/008276 WO2020009519A1 (ko) 2018-07-05 2019-07-05 다환 화합물 및 이를 포함하는 유기 발광 소자

Country Status (3)

Country Link
KR (1) KR102270475B1 (zh)
CN (1) CN112204026B (zh)
WO (1) WO2020009519A1 (zh)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020166630A1 (ja) * 2019-02-13 2020-08-20 保土谷化学工業株式会社 ベンゾアゾール環構造を有する化合物および有機エレクトロルミネッセンス素子

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210078992A1 (en) * 2018-07-05 2021-03-18 Lg Chem, Ltd. Polycyclic compound and organic light emitting diode comprising same
CN112300143B (zh) * 2019-07-30 2022-08-16 江苏三月科技股份有限公司 一种基于咔唑为核心的有机化合物及其应用
CN112851649B (zh) * 2019-11-28 2023-09-29 南京高光半导体材料有限公司 一种含有多元杂环结构的有机电致发光化合物及有机电致发光器件和应用
KR102170558B1 (ko) * 2020-03-12 2020-10-27 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기발광소자
KR102517278B1 (ko) * 2020-11-12 2023-04-05 주식회사 랩토 트리아진 또는 피리미딘 유도체, 및 이를 포함한 유기전계발광소자
CN113336744B (zh) * 2021-06-23 2024-04-26 长春海谱润斯科技股份有限公司 一种杂环衍生物及其有机电致发光器件
CN113527280B (zh) * 2021-07-09 2024-04-16 长春海谱润斯科技股份有限公司 一种杂环类化合物及其有机电致发光器件
CN113845512B (zh) * 2021-09-18 2023-05-05 长春海谱润斯科技股份有限公司 一种包含杂环的化合物及其有机电致发光器件
CN113816921B (zh) * 2021-09-23 2023-12-19 长春海谱润斯科技股份有限公司 一种杂环类化合物及其有机电致发光器件
CN114149361B (zh) * 2021-12-17 2024-01-26 长春海谱润斯科技股份有限公司 一种杂环衍生物及其有机电致发光器件

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012091026A1 (ja) * 2010-12-27 2012-07-05 東ソー株式会社 １，３，５－トリアジン化合物とその製造方法、及びそれらを構成成分とする有機電界発光素子
KR20130118269A (ko) * 2012-04-19 2013-10-29 에스에프씨 주식회사 방향족 화합물 및 이를 포함하는 유기전계발광소자
KR20150093440A (ko) * 2014-02-07 2015-08-18 롬엔드하스전자재료코리아유한회사 유기 전계 발광 소자
KR20160108798A (ko) * 2015-03-06 2016-09-20 삼성디스플레이 주식회사 유기 발광 소자
WO2016197353A1 (en) * 2015-06-11 2016-12-15 Dow Global Technologies Llc Organic electroluminescent compound and organic electroluminescent device comprising the same

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101741415B1 (ko) * 2009-04-29 2017-05-30 롬엔드하스전자재료코리아유한회사 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자
CN109206420B (zh) * 2017-12-14 2022-08-02 江苏三月科技股份有限公司 一种基于三嗪的有机化合物及其在有机电致发光器件上的应用
EP3533788A1 (en) * 2018-02-28 2019-09-04 Novaled GmbH Organic material for an electronic optoelectronic device and electronic device comprising the organic material
WO2019231212A1 (ko) * 2018-05-29 2019-12-05 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012091026A1 (ja) * 2010-12-27 2012-07-05 東ソー株式会社 １，３，５－トリアジン化合物とその製造方法、及びそれらを構成成分とする有機電界発光素子
KR20130118269A (ko) * 2012-04-19 2013-10-29 에스에프씨 주식회사 방향족 화합물 및 이를 포함하는 유기전계발광소자
KR20150093440A (ko) * 2014-02-07 2015-08-18 롬엔드하스전자재료코리아유한회사 유기 전계 발광 소자
KR20160108798A (ko) * 2015-03-06 2016-09-20 삼성디스플레이 주식회사 유기 발광 소자
WO2016197353A1 (en) * 2015-06-11 2016-12-15 Dow Global Technologies Llc Organic electroluminescent compound and organic electroluminescent device comprising the same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020166630A1 (ja) * 2019-02-13 2020-08-20 保土谷化学工業株式会社 ベンゾアゾール環構造を有する化合物および有機エレクトロルミネッセンス素子

Also Published As

Publication number Publication date
CN112204026A (zh) 2021-01-08
KR20200005489A (ko) 2020-01-15
KR102270475B1 (ko) 2021-06-29
CN112204026B (zh) 2024-05-07

Similar Documents

Publication Publication Date Title
WO2020009519A1 (ko) 다환 화합물 및 이를 포함하는 유기 발광 소자
WO2017043887A1 (ko) 유기전계발광소자
WO2020027389A1 (ko) 유기발광 화합물 및 이를 포함하는 유기발광소자
WO2017179911A1 (ko) 화합물 및 이를 포함하는 유기 전자 소자
WO2020009492A1 (ko) 다환 화합물 및 이를 포함하는 유기 발광 소자
WO2017061779A1 (ko) 아민 화합물 및 이를 포함하는 유기 발광 소자
WO2014123369A1 (ko) 신규한 화합물 및 이를 이용한 유기 전자 소자
WO2020171532A1 (ko) 화합물 및 이를 포함하는 유기 발광 소자
WO2019160315A1 (ko) 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
WO2019190230A1 (ko) 화합물 및 이를 포함하는 유기 발광 소자
WO2019240532A1 (ko) 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
WO2019013526A1 (ko) 신규한 화합물 및 이를 포함하는 유기 발광 소자
WO2019022499A1 (ko) 플루오렌 유도체 및 이를 포함하는 유기 발광 소자
WO2019143223A9 (ko) 다환 화합물 및 이를 포함하는 유기 발광 소자
WO2019143224A1 (ko) 다환 화합물 및 이를 포함하는 유기 발광 소자
WO2017171375A1 (ko) 화합물 및 이를 포함하는 유기 전자 소자
WO2022031028A1 (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
WO2022031013A1 (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
WO2022031016A1 (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
WO2022010087A1 (ko) 화합물 및 이를 포함하는 유기 발광 소자
WO2021040467A1 (ko) 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자
WO2022131575A1 (ko) 유기 화합물 및 이를 포함하는 유기발광소자
WO2020171530A1 (ko) 화합물 및 이를 포함하는 유기 발광 소자
WO2020180005A1 (ko) 바이나프탈렌 화합물 및 이를 포함하는 유기 발광 소자
WO2020149656A1 (ko) 신규한 화합물 및 이를 이용한 유기발광 소자

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 19830044

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 19830044

Country of ref document: EP

Kind code of ref document: A1